Phenylmethanesulfonyl chloride → (3S)-4-[[1-[(1-amino-6-isoquinolinyl)methyl]-2-oxo-2-(1-piperidinyl)ethyl]amino]-3-[[(phenylmethyl)sulfonyl]amino]-4-oxo-butanoic acid 1,1-dimethylethylester hydrochloride

HRID 1008510Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1008510
Cl.NC1C2C(=CC(CC(NC(=O)CNS(C3C(C)=C(C)C4OC(C)(C)CCC=4C=3C)(=O)=O)C(=O)N3CCCCC3)=CC=2)C=CN=1.[NH2:46][C:47]1[C:56]2[C:51](=[CH:52][C:53]([CH2:57][CH:58]([NH:67]C(=O)OC(C)(C)C)[C:59](=[O:66])[N:60]3[CH2:65][CH2:64][CH2:63][CH2:62][CH2:61]3)=[CH:54][CH:55]=2)[CH:50]=[CH:49][N:48]=1.[CH3:75][C:76]([O:79][C:80](=[O:97])[CH2:81][C@H:82]([NH:86][S:87]([CH2:90][C:91]1[CH:96]=[CH:95][CH:94]=[CH:93][CH:92]=1)(=[O:89])=[O:88])[C:83](O)=[O:84])([CH3:78])[CH3:77].N[C@H](C(O)=O)CC(=O)OC(C)(C)C.C1(CS([Cl:121])(=O)=O)C=CC=CC=1>>[ClH:121].[CH3:78][C:76]([O:79][C:80](=[O:97])[CH2:81][C@H:82]([NH:86][S:87]([CH2:90][C:91]1[CH:96]=[CH:95][CH:94]=[CH:93][CH:92]=1)(=[O:89])=[O:88])[C:83]([NH:67][CH:58]([CH2:57][C:53]1[CH:52]=[C:51]2[C:56](=[CH:55][CH:54]=1)[C:47]([NH2:46])=[N:48][CH:49]=[CH:50]2)[C:59](=[O:66])[N:60]1[CH2:61][CH2:62][CH2:63][CH2:64][CH2:65]1)=[O:84])([CH3:75])[CH3:77]

Komponenten

6

Edukt 5

HCID 74740Phenylmethanesulfonyl chlorideHCID 70105704-tert-Butyl hydrogen L-aspartateHCID 226656071,1-Dimethylethyl 1-[(1-amino-6-isoquinolinyl)methyl]-2-oxo-2-(1-piperidinyl)ethyl-carbamateHCID 22665631N-[1-[(1-Amino-6-isoquinolinyl)methyl]-2-oxo-2-(1-piperidinyl)ethyl]-2-[[(3,4-dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-yl)sulfonyl]amino]acetamide hydrochlorideHCID 69780511(2S)-[[(phenylmethyl)sulfonyl]amino]butanedioic acid 4-(1,1-dimethylethyl)ester

Produkt 1

HCID 69780956(3S)-4-[[1-[(1-amino-6-isoquinolinyl)methyl]-2-oxo-2-(1-piperidinyl)ethyl]amino]-3-[[(phenylmethyl)sulfonyl]amino]-4-oxo-butanoic acid 1,1-dimethylethylester hydrochloride

Versuchsvorschrift

The procedure described for 5c was used. Deprotection of 100 mg of 5a and coupling with 95 mg of (2S)-[[(phenylmethyl)sulfonyl]amino]butanedioic acid 4-(1,1-dimethylethyl)ester (prepared from Asp(OtBu)-OH and phenylmethylsulfonylchloride using the procedure described for 5b) yielded the title compound (133 mg) as a mixture of diastereomers (1:1). 1H-NMR 400 MHz (CD3OD) δ: 0.83-1.69 (6H, m), 1.41 and 1.42 (9H, 2× s), 2.42-2.63 (2H, m), 3.09-3.61 (6H, m), 4.01-4.38 (3H, m), 5.22-5.31 (1H, m), 7.13-7.80 (9H, m), 8.25-8.30 (1H, m).

Quellen und Nachweise

ORD-Eintrag
ord-5bf292f620b042dcbfd03d7dd059bc81
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06797710B2

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